6308-90-3

Usage

InChI:InChI=1/C9H14O4/c1-2-13-8(11)9(12)6-4-3-5-7(9)10/h12H,2-6H2,1H3

Upstream product

• 101455-38-3 ethyl 1,5-dithiaspiro-<5.5>-undecanyl-6-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 100-42-5 styrene 
• 110890-48-7 (1-Hydroxycyclopentyl)oxoacetic acid ethyl ester 

Downstream Products

• 1613315-43-7 (1-(tert-butyldimethylsilyloxy)-2-oxocyclohexyl)methyl 2-bromoacetate 
• 1613315-48-2 (1-(tert-butyldimethylsilyloxy)-2-oxocyclohexyl)methyl acetate 
• 1613315-40-4 ethyl 1,2-bis(tert-butyldimethylsilyloxy)cyclohex-2-enecarboxylate 
• 1613315-42-6 2-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)cyclohexanone 

Relevant academic research and scientific papers

Catalysis by Di-n-butyltin Oxide of a Tertiary Ketol Rearrangement: Synthesis of Intermediates and Analogues of Valine and Isoleucine Biosynthesis

Di-n-butyltin oxide efficiently catalyses the rearrangement of 3-hydroxy-2-oxocarboxylic acid ester into the corresponding 2-hydroxy-3-oxo-esters, in a reaction that simulates the reversible rearrangement catalysed by the enzyme reductoisomerase.

Formation of δ-Lactones by Cerium-Catalyzed, Baeyer-Villiger-Type Coupling of β-Oxoesters, Enol Acetates, and Dioxygen

Formation of δ-lactones is observed when cyclopentanone-2-carboxylates are converted in a cerium-catalyzed reaction with α-aryl vinyl acetates under oxidative conditions. The products of this transformation possess a 1,4-dicarbonyl constitution together with a quaternary carbon center. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C-C coupling and oxidation reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl3·7 H2O as precatalyst. This so far unprecedented reaction is proposed to proceed via 1,2-dioxane derivatives, which decompose under formation of an oxycarbenium cation in a Baeyer-Villiger-type pathway. This mechanistic picture is supported by the observation that electron-rich (donor substituted or heteroaromatic) enol esters give higher yields than electron deficient congeners. Apart from 1,4-diketones and α-hydroxylated β-oxoesters formed as byproducts, the yields of δ-lactones range from moderate to good (up to 74%).

Oxidative Chlorination of Activated Methylene Compounds with Sodium Chloride

An operationally simple protocol for the direct chlorination of 1,3-dicarbonyls (and related compounds such as α-cyano A?ketones) is described. The procedure relies on mild conditions using IBX-SO3K as the stoichiometric oxidizing agent and the

Novel oxygenations with IBX

Universal remedy: The α-hydroxylation of β-keto esters and a range of other suitably substituted carbonyl compounds can be effected in the presence of IBX (2-iodoxybenzoic acid). This novel reactivity underscores the importance of IBX as a universally applicable oxidizing agent.

Cerium-Catalyzed Reaction of β-Dicarbonyl Compounds with Styrene and Atmospheric Oxygen

The cerium-catalyzed C-C coupling reaction of carbo- and heterocyclic β-dicarbonyl compounds 1 with styrenes 4, using oxygen (air) as the oxidant, at ambient temperature, is reported. The reaction afforded a mixture of diastereoisomeric hydroperoxides 5 w

Preparation of acyloins by cerium-catalyzed, direct hydroxylation of β-dicarbonyl compounds with molecular oxygen

We report the metal-catalyzed α-hydroxylation of a variety of cyclic and acyclic β-dicarbonyl compounds by molecular oxygen. The decisive advantage of this new method is the use of catalytic amounts of the nontoxic cerium salt CeCl3·7H2O in 2-propanol at ambient temperature. Most of the cyclic substrates 4a-4i give high yields of analytically pure products 5a-5i, and the workup procedure is simple filtration through silica gel. The oxidation of acyclic dicarbonyl compounds 4j-4p, however, is accompanied by side reactions and decomposition, reducing the yields of products 5j-5p significantly. A proposed mechanism is in agreement with experimental results, in particular the observed oxygen uptake. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Cerium-catalyzed α-oxidation of β-dicarbonyl compounds with molecular oxygen

β-Ketoesters and β-diketones are α-hydroxylated by molecular oxygen in the presence of 5 mol% CECl3-7 H2O in i-PrOH as solvent. The method is limited to substrates with an α-alkyl substituent. Optimal yields are achieved with cyclic